Formaldehyde → HCID 19600111, compound

HRID 611240Notes

Reaction equation

HRID 611240 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:15]=[CH:14][O:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]=O>C(O)(=O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2[CH:15]=[CH:14][O:13][C:12]=2[CH2:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 19600250HCID 19600250, compound

Product 1

HCID 19600111HCID 19600111, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5.603 g (27.838 mmol) of N-benzyl-2-(3-furyl)ethylamine in 50 ml of acetic acid, 2.71 g (33.4 mmol) of 37% aqueous formaldehyde was added, followed by stirring at 100° C. for 1 hour. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-5fbee235727342598dcf324d0864cc4c
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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